1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose

Base Information

• Chemical Name: 1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose
• CAS No.: 88405-94-1
• Molecular Formula: C₃₉H₄₈O₁₁
• Molecular Weight: 692.804
• Mol file: 88405-94-1.mol

Synonyms:1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose

Chemical Property of 1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose

There total 8 articles about 1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

1,2:5,6-di-O-isopropylidene-α-D-galactofuranose (10368-86-2) + 1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose (74372-90-0,112289-38-0,135202-48-1,148888-66-8,71696-32-7) → 1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose (88405-94-1)

Guidance literature:

1,2:5,6-di-O-isopropylidene-α-D-galactofuranose; With bis(4-fluorophenyl)(hydroxy)borane; In toluene; for 3h; Inert atmosphere; Reflux;

1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose; In toluene; acetonitrile; at 0 ℃; for 24h; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.orglett.6b00926

Reference yield: 66.0%

1,2:5,6-di-O-isopropylidene-3-O-<3,4,6-tri-O-benzyl-2-O-(methylsulfonyl)-β-D-mannopyranosyl>-α-D-glucofuranose (88405-93-0) → 1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose (88405-94-1)

Guidance literature:

With sodium amalgam; In diethyl ether; isopropyl alcohol; Ambient temperature;

DOI:10.1016/0008-6215(83)88490-0

Reference yield:

3,4,6-tri-O-benzyl-D-mannopyranose (20672-66-6) → 1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose (88405-94-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / 2,6-lutidine / CH₂Cl₂ / 72 h

2: acetonitrile / 1 h / Ambient temperature

3: 0.2539 g / acetonitrile / 84 h / Ambient temperature

4: 66 percent / 6.88percent sodium amalgam / propan-2-ol; diethyl ether / Ambient temperature

With 2,6-dimethylpyridine; sodium amalgam; In diethyl ether; dichloromethane; isopropyl alcohol; acetonitrile;

DOI:10.1016/0008-6215(83)88490-0

upstream raw materials:

1,2:5,6-di-O-isopropylidene-3-O-<3,4,6-tri-O-benzyl-2-O-(methylsulfonyl)-β-D-mannopyranosyl>-α-D-glucofuranose

Acetic acid (3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-3-yl ester

Benzoic acid (3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-3-yl ester

3,4,6-tri-O-benzyl-D-mannopyranose